Jenny and I didn’t know that those three weeks in Southern California in 1996 would be our first trip of many. That 26 years later, we’d be packing our bags for a staycation at a Boulder hotel to celebrate what was unthinkable to us at the time: her pregnancy, created in a doctor’s office, costing unfair amounts of money, and done entirely, achingly, alone.

We only knew that adulthood and babies and, sigh, relationships, were still out there. Beyond our 15-year-old grasps, but floating toward us under a veil of limitless possibility and euphoric certainty. Not among our possibilities? Single parenthood. The reality neither of us had considered but that we’d both, to varying degrees, face.

California

Jenny and I met in a seventh-grade Spanish class in 1993. Three years later, were traveled together for our first taste of freedom.

She boarded a plane from Denver with me, just the two of us, carrying on a 5-pound bag of gummy bears, a deck of cards, and the lightness of being away from our mothers for the first time in our lives. We were going to stay with my dad over the summer, and since he’d never been a full-time parent and had no idea what to do with two teenage girls, we’d fumble along together to make the rules.

Most teenagers would probably have taken advantage of this fathering handicap. Maybe they’d sneak out to find a party, wear more makeup than their mothers would have allowed or find someone to buy them beer. Our main act of debauchery was going out for ice cream a little late without telling my dad.

I desperately wanted a boyfriend, but wouldn’t get one for another few years. Jenny, at least, had been on dates, and she seemed (and was) so much cooler than me. Even as a teenager, she was a confident person who radiated so much energy that everyone was drawn to her. Everyone wanted to be friends with her, and I often wondered why she chose me, someone without that confidence and coolness.

I wanted to be someone else back then. Someone who was wanted by boys, because, growing up in the “90210” days, I thought that’s what being a teenage girl was supposed to be. Without a sense of my own worth, I needed to see it reflected back at me via male approval — something that would take me the next couple of decades to understand and dismantle. I was genuinely surprised, and almost constantly depressed, when my high school years didn’t look like Brenda Walsh’s.

Nobody kissed anyone in California, but it was coming, right? It had to be.

Costa Rica

I finally got that seal of approval — or, rather, that boyfriend — in college. He was kind and lovely and so was I, but I was also too young and had too much to learn about, well, everything. Just after we’d all graduated from college and I started law school, almost 20 years ago, I broke his heart. I guess I didn’t want to be a wife just then after all, and I definitely didn’t want to be a lawyer. So I ended both law school and my relationship with him over the course of a very painful two-day period. Sitting in Jenny’s childhood bedroom — a room I’d spent so much time in that it was my teeth marks on the rubber spiral phone cord — we decided to take another trip.

The timing felt urgent; the impending adulthood we weren’t quite ready to face was closing in on us at 22. Being kids was still a recent memory, not the distant one it is now, and thank God we booked a plane ticket to Costa Rica that week to touch and feel what it was like one last time.

Jenny picked Costa Rica because the beaches looked nice, she wanted to put our high school Spanish into action and, in 2003, it was still cheap enough that our graduation checks and college job savings could cover the $5-a-night cabinas we’d sleep in. Very few people understood why I chose to go through the upheaval of the life it was looking like I’d lead. But Jenny did. Always up for a trip, an adventure, a new experience, we went together. Adulthood would be waiting for us in Colorado when we got back, a couple of months later.

Maybe it was in Costa Rica that Jenny told me she’d always visualized herself as being a mom — but never foresaw herself as a wife. Still, the reality of that dichotomy is pretty darned daunting. To intentionally do it on your own. Without built-in child care or support — financially or otherwise — without knowing who the other half of your child is.

I couldn’t think about children yet, being so close to one myself. I just thought about the jungle, the waves and the crushing pain of knowing you broke someone you love.

Jamaica

Four years later, we boarded another plane together, this one headed to my wedding in Negril, Jamaica. Jenny, newly broken up with her boyfriend, had gotten ordained in order to marry me and Peter. I wasn’t nervous about marrying that wonderful man, but still I cried and threw up all week, worried about the weather, if my parents would get along, and all the stupid little wedding details that truly don’t matter but seemed so critically important at the time.

That’s what I remember most about my wedding week: crying. I cried when Jenny and I didn’t win the scavenger hunt game we all played. I cried fighting with Peter after the very drunken rehearsal dinner, standing outside our room on the cliffs of Negril, with the Caribbean pounding below us. I cried so much that week that I stopped crying after that. My emotional switch flipped to the “off” position, and it took the dissolution of that marriage more than a decade later to flip it back on.

Jenny jumped into the Caribbean Sea off a 40-foot cliff on that trip. I walked down an aisle in a white dress.

Wyoming, Kansas, Nebraska

In our late 20s, when life got busier, we started taking Mystery Road Trips. We’d block out a day or two over a weekend, grab The Wheel (a red piece of construction paper with a makeshift spinner pinned to the middle), and spin. We’d give it a whirl to see which direction we’d drive, what highway we’d get off on, how far we’d go before turning, and so on. Without a destination in mind, we could have ended up anywhere. But with a five-hour drive limit, “anywhere” tended to be Wyoming, Nebraska or Kansas.

We were looking for some sort of adventure, a quick diversion, a dip into life in what was usually a small, rural town. Mystery Road Trips broke up the monotonous rut that sometimes took over my existence, when even vacations seemed calculated. Not knowing where we’d end up made me giddy again, and I needed to feel giddy. It was the not knowing where we were going that was so seductive.

Because of The Wheel, we met ranchers, singers, baseball umpires and an honest-to-God psychic/peacock farmer. We met “Mom” and her two boys in Dalhart, Texas, who taught us to shoot a gun — you know, just in case. We climbed on tractors in the hot, sticky Wyoming summer night, because that’s what city girls do when in Wyoming. We went to Colby, Kan., when I was pregnant and newly 30, and all I remember is sitting in a bar, sober, amid some sort of high school reunion.

With The Wheel, I got more comfortable with the unknown. Maybe Jenny did, too. I went into these journeys believing that I didn’t have a lot of choices when it came to my life. I had to go to the job I disliked. I had to do a certain number of chores to prove I was a good mother and wife. The Wheel reminded me that I really could go anywhere and do anything on any given day. That the perimeters of our lives are expandable.

Florida

Peter and I separated in August 2018 and the pain was almost more than I could handle. After seven months of soothing the children and soothing myself, Jenny and I took ourselves on an adult spring break. We slept in a sailboat parked in Cow Key, Fla. We didn’t have plumbing, refrigeration or so much as a foot above our heads in our tiny, humid sleeping quarters.

It was the best place in which either of us has ever stayed.

The children had needed me so much, but probably not as much as I needed them. Learning to cook for them, getting them to school and back at the same time each day, and keeping our household running on my own had been the routine saving graces that kept me from succumbing to the hopelessness and depression. The tears had come back, violently racking my body when no one was looking.

But for that week, there was no one to take care of but myself. No small bodies clung to my own, breaking my already broken heart. Without the responsibility of what I needed to do, I found some joy in what I wanted to do. I could be happy again, I realized on our little sailboat. I could do many things, actually, that I didn’t think were possible.

Maybe the sailboat inspired new possibilities for Jenny, too. She debated adoption versus IVF as we sliced through glassy waters on our kayak, searching for manatees, nurse sharks and answers. I kissed a man who was not my husband in Key Largo. The world opened up for both of us.

Hawaii

During the pandemic, Jenny solidified her decision to have a baby on her own. She’d chosen a sperm donor and would start the IVF process as soon as we got home from the Big Island. This was a last hurrah trip or, if not the last, a pause of the trips.

The first real relationship I’d had post-divorce looked like it was ending. Days before we left, my boyfriend checked into rehab for alcohol addiction. I didn’t know what would happen next, and I didn’t believe he could be sober. But I didn’t want to be someone else anymore; I didn’t need to be wanted by boys. I didn’t want a 90210 life, and I didn’t need my worth reflected back to me via male approval. And so I removed myself from that situation and went to Hawaii with my best friend.

We snorkeled all day, every day. She, fully enjoying her unencumbered lifestyle one last time, and me, finding a sense of peace and stillness that took me out of the turbulence. We drank grocery store sake and named (and then forgot what we named) her future baby. I avoided early-morning calls from the psychiatrist at the rehab center. She took her top off at a nude beach for the first time.

Boulder

Of course it’s not that there aren’t loads of single parents, especially mothers, out there. My own mother was one, and while my ex-husband is a very involved father, when we parent, it’s separately. Alone. The difference in origins between most single parents, though, and Jenny, is that we didn’t set out to do it this way. It happened accidentally, like in the case of my mother, or something happened to sever the relationship we thought would last forever.

It’s not as rare as it used to be, though. The number of women choosing to become moms with the help of science and without the help of a romantic partner is on the rise. It takes a lot of gumption, endurance and, yes, money, to do it this way. It is what Jenny and so many other good moms have done.

A couple of months before her due date, I realized that Jenny wouldn’t get a babymoon, the trip that many couples take pre-baby to bond before their lives become all baby, all the time. Peter and I had gone to Portland, Ore., on the cusp of my third trimester, and it seemed unfair that she wouldn’t get a trip because she didn’t have a partner.

She didn’t want to travel far that close to her due date, so I booked us a quick babymoon in Boulder. We stayed at the St. Julien, a property much classier than the cheap sort of motels we normally picked. We ate a ridiculously expensive dinner at Frasca, one of the state’s best restaurants. And then we downloaded a sports betting app and spent the rest of the time in the room betting on minor league hockey games we knew nothing about.

Jenny had her baby five days before Mother’s Day. Her daughter has shaken free emotions and love in Jenny that, in 25 years, I’ve never seen in her. Kids do that.

On Mother’s Day morning, my boyfriend — the one who became and has remained sober — brought pancakes and my children up to my bed and asked me to marry him. He’d asked the kids for their permission the night before.

Jenny’s single motherhood has just begun and mine, it appears, has ended.

Adulthood, babies and relationships are here. That veil of limitless possibility and euphoric certainty floating toward me at 15 has reached me, and I, like every other adult, have tossed it to the side, opening my eyes instead to the pain, joy and uncertainty of real life.

But I can always pack my bags. I can always change the scenery. There are always more trips, and I have a friend to join me.

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